# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv382
_database_code_depnum_ccdc_archive 'CCDC 1446302'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 I2 N3'
_chemical_formula_sum            'C3 H3 I2 N3'
_chemical_formula_weight         334.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.4559(8)
_cell_length_b                   4.1982(3)
_cell_length_c                   7.7048(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     370.56(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3040
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.001
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    8.396
_shelx_estimated_absorpt_T_min   0.135
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.4936
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            3581
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.186
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             838
_reflns_number_gt                830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.878
_reflns_Friedel_fraction_full    0.899

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_refine_ls_number_reflns         838
_refine_ls_number_parameters     41
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0453
_refine_ls_wR_factor_gt          0.0452
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82126(2) 0.55476(6) 0.49424(11) 0.02175(13) Uani 1 1 d . . . . .
C2 C 0.9391(3) 0.3625(12) 0.6689(7) 0.0159(8) Uani 1 1 d . . . . .
N3 N 0.9016(3) 0.2128(10) 0.8104(5) 0.0189(8) Uani 1 1 d . . . . .
N4 N 1.0000 0.1251(15) 0.8897(8) 0.0170(11) Uani 1 2 d S T P . .
C5 C 1.0000 -0.0361(19) 1.0567(12) 0.0261(17) Uani 1 2 d S T P . .
H5A H 1.0805 -0.0839 1.0909 0.039 Uiso 0.5 1 calc R U P . .
H5B H 0.9556 -0.2349 1.0476 0.039 Uiso 0.5 1 calc R U P . .
H5C H 0.9639 0.1019 1.1441 0.039 Uiso 0.5 1 calc R U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02029(17) 0.02361(19) 0.0213(2) 0.0028(3) -0.00604(13) 0.00042(7)
C2 0.0128(19) 0.0186(19) 0.016(2) -0.0006(19) -0.0026(17) 0.0007(16)
N3 0.0154(17) 0.0236(19) 0.018(2) -0.0002(17) -0.0013(15) 0.0021(13)
N4 0.016(2) 0.017(2) 0.018(3) 0.000(2) 0.000 0.000
C5 0.030(4) 0.025(4) 0.023(4) 0.007(3) 0.000 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.070(5) . ?
C2 N3 1.329(7) . ?
C2 C2 1.396(8) 3_755 ?
N3 N4 1.334(5) . ?
N4 N3 1.334(5) 3_755 ?
N4 C5 1.454(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C2 C2 108.8(2) . 3_755 ?
N3 C2 I1 120.5(3) . . ?
C2 C2 I1 130.69(13) 3_755 . ?
C2 N3 N4 103.5(4) . . ?
N3 N4 N3 115.3(6) 3_755 . ?
N3 N4 C5 122.3(3) 3_755 . ?
N3 N4 C5 122.3(3) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C2 N3 N4 -0.6(4) 3_755 . . . ?
I1 C2 N3 N4 -179.7(4) . . . . ?
C2 N3 N4 N3 1.1(7) . . . 3_755 ?
C2 N3 N4 C5 177.1(6) . . . . ?

_refine_diff_density_max         0.816
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.166

# start Validation Reply Form
_vrf_PLAT015_shrv382             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv381
_database_code_depnum_ccdc_archive 'CCDC 1446304'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 I2 N3'
_chemical_formula_sum            'C4 H5 I2 N3'
_chemical_formula_weight         348.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.274(3)
_cell_length_b                   7.508(3)
_cell_length_c                   7.980(3)
_cell_angle_alpha                84.239(4)
_cell_angle_beta                 83.370(5)
_cell_angle_gamma                68.174(4)
_cell_volume                     401.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4001
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      30.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.889
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    7.763
_shelx_estimated_absorpt_T_min   0.193
_shelx_estimated_absorpt_T_max   0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.3924
_exptl_absorpt_correction_T_max  0.7461

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
__diffrn_radiation_source        'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2117
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.928
_diffrn_reflns_theta_max         30.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2117
_reflns_number_gt                1945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+2.5494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2845(9) -0.1443(9) 0.8798(8) 0.0250(12) Uani 1 1 d . . . . .
H1A H 0.3236 -0.0602 0.9426 0.037 Uiso 1 1 calc R U . . .
H1B H 0.3908 -0.2714 0.8765 0.037 Uiso 1 1 calc R U . . .
H1C H 0.1624 -0.1570 0.9359 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2483(8) -0.0582(8) 0.7008(7) 0.0199(10) Uani 1 1 d . . . . .
H2B H 0.3735 -0.0526 0.6415 0.024 Uiso 1 1 calc R U . . .
H2A H 0.2039 -0.1403 0.6383 0.024 Uiso 1 1 calc R U . . .
N3 N 0.0950(6) 0.1376(6) 0.7042(6) 0.0156(8) Uani 1 1 d . . . . .
N4 N -0.0977(7) 0.1615(7) 0.7019(6) 0.0194(9) Uani 1 1 d . . . . .
N5 N -0.2019(7) 0.3472(7) 0.7140(6) 0.0187(9) Uani 1 1 d . . . . .
C6 C -0.0751(8) 0.4386(8) 0.7252(6) 0.0175(10) Uani 1 1 d . . . . .
I7 I -0.16213(5) 0.73154(5) 0.74535(4) 0.01934(11) Uani 1 1 d . . . . .
C8 C 0.1159(8) 0.3069(7) 0.7195(6) 0.0160(9) Uani 1 1 d . . . . .
I9 I 0.38693(5) 0.33827(5) 0.71751(4) 0.01672(10) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.019(3) 0.022(3) 0.030(3) 0.001(2) -0.007(2) -0.002(2)
C2 0.014(3) 0.019(3) 0.027(3) -0.0003(19) -0.0021(19) -0.007(2)
N3 0.009(2) 0.014(2) 0.023(2) -0.0017(15) -0.0026(15) -0.0020(16)
N4 0.012(2) 0.015(2) 0.029(2) 0.0006(17) -0.0027(17) -0.0030(17)
N5 0.012(2) 0.023(2) 0.022(2) 0.0010(17) -0.0043(16) -0.0066(18)
C6 0.015(3) 0.021(2) 0.018(2) 0.0000(18) -0.0004(18) -0.008(2)
I7 0.01452(19) 0.01482(17) 0.02648(19) -0.00255(12) -0.00226(13) -0.00236(13)
C8 0.015(3) 0.013(2) 0.019(2) -0.0019(17) 0.0007(18) -0.0047(19)
I9 0.00919(17) 0.01637(17) 0.02514(18) -0.00229(12) -0.00234(11) -0.00479(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.518(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N3 1.479(7) . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
N3 N4 1.347(6) . ?
N3 C8 1.354(7) . ?
N4 N5 1.324(7) . ?
N5 C6 1.353(7) . ?
C6 C8 1.372(8) . ?
C6 I7 2.068(6) . ?
C8 I9 2.069(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 C1 110.0(5) . . ?
N3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
N3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
H2B C2 H2A 108.2 . . ?
N4 N3 C8 111.2(4) . . ?
N4 N3 C2 119.5(4) . . ?
C8 N3 C2 129.2(5) . . ?
N5 N4 N3 106.9(4) . . ?
N4 N5 C6 108.7(5) . . ?
N5 C6 C8 109.2(5) . . ?
N5 C6 I7 124.2(4) . . ?
C8 C6 I7 126.5(4) . . ?
N3 C8 C6 104.0(5) . . ?
N3 C8 I9 124.1(4) . . ?
C6 C8 I9 131.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N3 N4 -90.6(6) . . . . ?
C1 C2 N3 C8 85.1(6) . . . . ?
C8 N3 N4 N5 0.6(6) . . . . ?
C2 N3 N4 N5 177.0(4) . . . . ?
N3 N4 N5 C6 -0.5(6) . . . . ?
N4 N5 C6 C8 0.2(6) . . . . ?
N4 N5 C6 I7 179.7(4) . . . . ?
N4 N3 C8 C6 -0.5(6) . . . . ?
C2 N3 C8 C6 -176.5(5) . . . . ?
N4 N3 C8 I9 -177.1(3) . . . . ?
C2 N3 C8 I9 6.9(8) . . . . ?
N5 C6 C8 N3 0.2(6) . . . . ?
I7 C6 C8 N3 -179.3(4) . . . . ?
N5 C6 C8 I9 176.5(4) . . . . ?
I7 C6 C8 I9 -3.0(7) . . . . ?

_refine_diff_density_max         1.489
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.218


# start Validation Reply Form
_vrf_PLAT015_shrv381             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv352
_database_code_depnum_ccdc_archive 'CCDC 1446331'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 I N4 O2'
_chemical_formula_sum            'C3 H3 I N4 O2'
_chemical_formula_weight         253.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0649(12)
_cell_length_b                   7.2001(12)
_cell_length_c                   7.8953(13)
_cell_angle_alpha                70.362(5)
_cell_angle_beta                 64.462(5)
_cell_angle_gamma                86.027(5)
_cell_volume                     339.95(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2179
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.481
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    4.654
_shelx_estimated_absorpt_T_min   0.423
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.4033
_exptl_absorpt_correction_T_max  0.7453

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2656
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         25.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1247
_reflns_number_gt                1155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+1.0194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1247
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2332(7) 0.6674(7) 0.2588(7) 0.0231(10) Uani 1 1 d . . . . .
N2 N 0.2579(8) 0.5615(7) 0.4182(7) 0.0247(10) Uani 1 1 d . . . . .
N3 N 0.2687(7) 0.3728(7) 0.4236(7) 0.0211(9) Uani 1 1 d . . . . .
C4 C 0.3049(11) 0.2249(9) 0.5836(9) 0.0289(13) Uani 1 1 d . . . . .
H4A H 0.4531 0.1968 0.5326 0.043 Uiso 1 1 calc R U . . .
H4B H 0.2151 0.1030 0.6325 0.043 Uiso 1 1 calc R U . . .
H4C H 0.2710 0.2755 0.6932 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2561(8) 0.3534(8) 0.2638(8) 0.0182(10) Uani 1 1 d . . . . .
I6 I 0.25974(5) 0.08334(5) 0.22311(5) 0.02182(16) Uani 1 1 d . . . . .
C7 C 0.2333(9) 0.5450(8) 0.1610(8) 0.0207(11) Uani 1 1 d . . . . .
N8 N 0.2147(8) 0.6194(7) -0.0231(7) 0.0249(10) Uani 1 1 d . . . . .
O9 O 0.1790(8) 0.7922(7) -0.0790(7) 0.0411(11) Uani 1 1 d . . . . .
O10 O 0.2409(7) 0.5055(7) -0.1163(6) 0.0322(10) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.034(2) 0.013(2) 0.025(2) -0.0082(19) -0.014(2) 0.0024(19)
N2 0.038(3) 0.018(2) 0.021(2) -0.0096(19) -0.013(2) 0.000(2)
N3 0.035(2) 0.015(2) 0.021(2) -0.0085(19) -0.0177(19) 0.0009(19)
C4 0.048(4) 0.022(3) 0.027(3) -0.008(2) -0.026(3) 0.004(3)
C5 0.027(3) 0.013(2) 0.020(3) -0.010(2) -0.011(2) 0.000(2)
I6 0.0327(2) 0.0158(2) 0.0237(2) -0.01254(15) -0.01383(16) 0.00286(14)
C7 0.028(3) 0.019(3) 0.020(3) -0.011(2) -0.011(2) 0.000(2)
N8 0.030(2) 0.023(3) 0.021(2) -0.004(2) -0.0122(19) -0.003(2)
O9 0.062(3) 0.021(2) 0.049(3) -0.001(2) -0.039(2) 0.001(2)
O10 0.045(2) 0.037(3) 0.022(2) -0.0138(19) -0.0175(18) 0.002(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.312(7) . ?
N1 C7 1.352(7) . ?
N2 N3 1.343(6) . ?
N3 C5 1.355(6) . ?
N3 C4 1.460(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C7 1.385(8) . ?
C5 I6 2.072(5) . ?
C7 N8 1.432(7) . ?
N8 O9 1.220(7) . ?
N8 O10 1.231(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 107.8(4) . . ?
N1 N2 N3 107.9(4) . . ?
N2 N3 C5 111.5(4) . . ?
N2 N3 C4 118.9(4) . . ?
C5 N3 C4 129.5(5) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C7 102.6(4) . . ?
N3 C5 I6 122.9(4) . . ?
C7 C5 I6 134.4(4) . . ?
N1 C7 C5 110.1(4) . . ?
N1 C7 N8 120.8(5) . . ?
C5 C7 N8 129.1(5) . . ?
O9 N8 O10 124.6(5) . . ?
O9 N8 C7 117.8(5) . . ?
O10 N8 C7 117.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 N3 -1.4(6) . . . . ?
N1 N2 N3 C5 1.4(6) . . . . ?
N1 N2 N3 C4 177.5(5) . . . . ?
N2 N3 C5 C7 -0.9(6) . . . . ?
C4 N3 C5 C7 -176.4(6) . . . . ?
N2 N3 C5 I6 -178.5(4) . . . . ?
C4 N3 C5 I6 6.0(8) . . . . ?
N2 N1 C7 C5 0.9(7) . . . . ?
N2 N1 C7 N8 -178.3(5) . . . . ?
N3 C5 C7 N1 0.0(6) . . . . ?
I6 C5 C7 N1 177.2(4) . . . . ?
N3 C5 C7 N8 179.1(5) . . . . ?
I6 C5 C7 N8 -3.7(9) . . . . ?
N1 C7 N8 O9 -6.7(8) . . . . ?
C5 C7 N8 O9 174.3(6) . . . . ?
N1 C7 N8 O10 171.6(5) . . . . ?
C5 C7 N8 O10 -7.5(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B O9 0.98 2.53 3.218(7) 126.9 1_546
C4 H4C O10 0.98 2.53 3.473(7) 161.8 1_556

_refine_diff_density_max         1.083
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.165

# start Validation Reply Form
_vrf_PLAT015_shrv352             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv380
_database_code_depnum_ccdc_archive 'CCDC 1446333'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 I N4 O2'
_chemical_formula_sum            'C4 H5 I N4 O2'
_chemical_formula_weight         268.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9327(11)
_cell_length_b                   7.2485(11)
_cell_length_c                   8.5638(12)
_cell_angle_alpha                77.511(5)
_cell_angle_beta                 67.263(4)
_cell_angle_gamma                83.499(5)
_cell_volume                     387.30(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2584
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      29.64

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.298
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.014
_exptl_absorpt_coefficient_mu    4.091
_shelx_estimated_absorpt_T_min   0.536
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.5756
_exptl_absorpt_correction_T_max  0.7460

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4209
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         30.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2103
_reflns_number_gt                1872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2103
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0508(5) 0.2797(5) 0.9263(5) 0.0254(7) Uani 1 1 d . . . . .
H1A H 0.0913 0.3855 0.8282 0.038 Uiso 1 1 calc R U . . .
H1B H -0.0668 0.3201 1.0224 0.038 Uiso 1 1 calc R U . . .
H1C H 0.0091 0.1744 0.8925 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2357(5) 0.2163(5) 0.9817(4) 0.0209(7) Uani 1 1 d . . . . .
H2A H 0.2799 0.3232 1.0136 0.025 Uiso 1 1 calc R U . . .
H2B H 0.1933 0.1133 1.0841 0.025 Uiso 1 1 calc R U . . .
N3 N 0.4125(4) 0.1488(4) 0.8398(3) 0.0167(5) Uani 1 1 d . . . . .
C4 C 0.5628(5) 0.2474(5) 0.7038(4) 0.0152(6) Uani 1 1 d . . . . .
I5 I 0.60751(3) 0.53070(3) 0.67905(2) 0.01876(8) Uani 1 1 d . . . . .
C6 C 0.6610(5) 0.1097(5) 0.6059(4) 0.0158(6) Uani 1 1 d . . . . .
N7 N 0.8307(4) 0.1303(4) 0.4398(3) 0.0190(5) Uani 1 1 d . . . . .
O8 O 0.9036(4) 0.2877(4) 0.3744(3) 0.0275(6) Uani 1 1 d . . . . .
O9 O 0.8916(4) -0.0115(4) 0.3755(3) 0.0252(5) Uani 1 1 d . . . . .
N10 N 0.5726(4) -0.0585(4) 0.6831(4) 0.0191(6) Uani 1 1 d . . . . .
N11 N 0.4193(4) -0.0353(4) 0.8271(3) 0.0204(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0195(16) 0.0267(19) 0.0243(17) -0.0081(15) 0.0000(13) -0.0014(14)
C2 0.0220(16) 0.0211(17) 0.0141(14) -0.0060(12) 0.0010(12) -0.0018(13)
N3 0.0185(13) 0.0149(13) 0.0129(12) -0.0023(10) -0.0017(10) -0.0016(10)
C4 0.0156(14) 0.0160(15) 0.0116(13) -0.0022(11) -0.0025(11) -0.0007(11)
I5 0.02296(13) 0.01375(12) 0.01772(11) -0.00301(8) -0.00448(8) -0.00454(8)
C6 0.0164(14) 0.0148(15) 0.0127(13) -0.0017(11) -0.0022(11) -0.0006(11)
N7 0.0191(13) 0.0211(14) 0.0148(12) -0.0031(11) -0.0048(10) 0.0010(11)
O8 0.0268(13) 0.0227(13) 0.0205(12) 0.0017(10) 0.0025(10) -0.0044(10)
O9 0.0253(13) 0.0277(14) 0.0205(11) -0.0120(11) -0.0035(9) 0.0036(11)
N10 0.0207(14) 0.0158(14) 0.0181(13) -0.0029(11) -0.0046(11) 0.0001(11)
N11 0.0227(15) 0.0151(14) 0.0189(13) -0.0024(11) -0.0024(11) -0.0039(11)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.524(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N3 1.479(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C4 1.351(4) . ?
N3 N11 1.356(4) . ?
C4 C6 1.389(4) . ?
C4 I5 2.064(3) . ?
C6 N10 1.344(4) . ?
C6 N7 1.444(4) . ?
N7 O8 1.227(4) . ?
N7 O9 1.227(4) . ?
N10 N11 1.310(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 C1 110.2(3) . . ?
N3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 N3 N11 111.7(2) . . ?
C4 N3 C2 129.8(3) . . ?
N11 N3 C2 118.0(3) . . ?
N3 C4 C6 101.9(3) . . ?
N3 C4 I5 123.3(2) . . ?
C6 C4 I5 134.8(2) . . ?
N10 C6 C4 111.1(3) . . ?
N10 C6 N7 120.4(3) . . ?
C4 C6 N7 128.5(3) . . ?
O8 N7 O9 125.1(3) . . ?
O8 N7 C6 117.6(3) . . ?
O9 N7 C6 117.3(3) . . ?
N11 N10 C6 107.6(3) . . ?
N10 N11 N3 107.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N3 C4 84.3(4) . . . . ?
C1 C2 N3 N11 -87.3(3) . . . . ?
N11 N3 C4 C6 0.6(4) . . . . ?
C2 N3 C4 C6 -171.5(3) . . . . ?
N11 N3 C4 I5 -178.6(2) . . . . ?
C2 N3 C4 I5 9.4(5) . . . . ?
N3 C4 C6 N10 -0.6(4) . . . . ?
I5 C4 C6 N10 178.3(2) . . . . ?
N3 C4 C6 N7 177.2(3) . . . . ?
I5 C4 C6 N7 -3.8(6) . . . . ?
N10 C6 N7 O8 179.0(3) . . . . ?
C4 C6 N7 O8 1.4(5) . . . . ?
N10 C6 N7 O9 -1.4(5) . . . . ?
C4 C6 N7 O9 -179.0(3) . . . . ?
C4 C6 N10 N11 0.5(4) . . . . ?
N7 C6 N10 N11 -177.5(3) . . . . ?
C6 N10 N11 N3 -0.1(4) . . . . ?
C4 N3 N11 N10 -0.3(4) . . . . ?
C2 N3 N11 N10 172.8(3) . . . . ?

_refine_diff_density_max         1.243
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.162

# start Validation Reply Form
_vrf_PLAT015_shrv380             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
